There is nothing like the excitement of visiting a place for the very first time.

If you are like me, you research like crazy, plan, prepare, reserve and count down the days until departure.

You do everything in your power to make sure the trip is smooth and enjoyable from the time you leave until the moment you return.

You probably pack some essentials like noise-canceling headphones, chargers and snacks for the plane rides and then start thinking about the “slightly-more-essential” things like underwear and deodorant.

Then, you piece together your Adventure Crew. You’re heading to a Spanish speaking country, right? Ok, taking your Spanish teacher brother would be a wise choice (any back up on translation is always welcome).

Include your 69 year old father-in-law who has a heart for adventure, also speaks Spanish and slight penchant for wandering off. Of course!

Oh, and let’s not forget to bring along your 64 year old father who also enjoys the occasional taste of adventure and comes fully equipped with two semi-new hips (hello, metal detectors), a Sesame Street-level knowledge of the Spanish language and a presence that intimidates most foreigners and you now have an unstoppable team.

And by unstoppable I mean the most random group of travelers ever assembled.

Once all of this is set, you remember Cuba is still a Communist, island country and prepare to throw all your plans out the window. This is trip is going to be different.


Our adventure started with a 4:30am wake-up call

and heading to the airport in the dark to be on time for our 7:15am flight. Of course, since there was no traffic to delay our drive we had to get stuck in the world’s longest detour thanks to all the construction off Loop 12. We laughed it off the best we could but this would definitely be a sign of things to come.

Our flights and time at the airports went smoothly with the exception of Ft. Lauderdale. For some reason they have decided to keep 4 gates in a nice little secure corner of the airport with few places to get food and ZERO functioning currency exchange booths or machines within. Not great when you are attempting to avoid a 10% added fee when exchanging dollars to CUC (Cuban currency). Ultimately, you take the hit, hope you have enough cash for your trip and move on.

We arrived in Cuba about 1:30pm and made our way through the security check in. A not-so-enthusiastic government employee checks your passport and then asks you to stand against the wall to take your photo. Then, they check their screen and realize they can pretty much only see your belt and ask you to squat down. I guess there are no panning features on their high tech security cameras but, hey, this IS Cuba.

Once you clear the security line and metal detectors (staffed completely by young ladies dressed in short khaki skirts and white shirts – yes, like Cuban fem-bots), you head over to the baggage claim area. This was not initially part of the plan, but my brother was caught with a duffle bag slightly exceeding the carry-on limit, so we had no choice.

I learned one thing during our 45-minute wait at those luggage carrousels…Cubans are anxious to get caught up on technology. As the crowd grew in size and impatience while waiting for a bag here and suitcase there to emerge from out of that mysterious hole in the wall, I noticed how about one of every five pieces was a giant box carrying at least a 55” TV. Not even kidding, they just kept coming out. After a few days, I started to understand though. It’s just hard to really enjoy the 1950’s black-and-white version of The Titanic on that 35” tube TV.

We exited the airport to a crowd of waiting friends, family and taxi drivers. None of them were there for us, but it was still kind of a rush.

Our driver must have taken a smoke break or gone to get a sandwich because he was nowhere to be found (Tim Chesney on a little white piece of paper is a fairly easy name to recognize in country with mostly Spanish surnames). Eventually Pipe (Pee-pay) showed up and we excitedly followed him to his car.

We marveled at the age and condition of many of the classics we passed and my father-in-law (a natural mechanic and car enthusiast) was having a blast identifying the makes, models and countries of origin of many of the vehicles we saw as we sped through Havana.

After 3 attempts at finding a currency exchange place, we found a hotel that offered the service and learned how spotty the internet can be when we were informed it was “out on the entire island”. I think this is where I just adopted my favorite coping phrase…”This is Cuba”.

We came upon our Airbnb home for the night soon afterward but not without what would be the customary stop and ask the actual location of any person sitting, standing, walking, working, smoking outside. House numbers are not easy to locate and streets/areas can be confusing even to taxi drivers.

After connecting with our host – who happened to be the cousin of the owner who actually lived in Madrid – we registered our passports (yep, has to be done at every location) and enjoyed a few moments of calm before heading out to Havana Vieja (Old Town) for some time to explore. We took in the architecture and did a little shopping while our host/guide, Moises, led us through the tourist crowded streets and showed us places like the bar Hemingway frequented for his favorite Mojitos during his time in Cuba. It was fascinating. We soaked it all in and even enjoyed some time walking the Malecón (seawall/big sidewalk/local hangout area) before heading back to our place for the evening and turning in.

It was a day filled with sitting in cars, cabs and airplanes with some sightseeing sprinkled in and a little local frustration as well, but overall pretty good first day of our trip.

What we didn’t know, at the time, was this was going to be the smoothest and least “Cuban” day of our entire time in this country.

The adventure was just beginning.

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